Following tools will help you detecting outdated software.
Mint update from 18.3 to 19 – Wine broke
After updating from Linux Mint 18.3 to 19, wine stopped working. This is what was required to correct.
sudo all below commands if required
dpkg --add-architecture i386
apt-add-repository 'deb https://dl.winehq.org/wine-builds/ubuntu/ bionic main'
wget -nc https://dl.winehq.org/wine-builds/Release.key
apt-key add Release.key
Check if you do not have duplicate lines from an earlier install.
vi /etc/apt/sources.list.d/additional-repositories.list
Then the final step.
apt-get update
reboot
apt-get install --install-recommends winehq-stable
Source: Ubuntu – WineHQ Wiki